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Pre-heat oven to 425 degrees F with two sheet trays inside. Slice a small piece off the ends of the sprouts and then slice them in half. Add sprouts to a bowl and season them with 1 tablespoon of oil, just under 1 teaspoon of salt, a few cracks of pepper, and mix well. Carefully cut the squash in half from top to bottom(no need to peel) and use a spoon to scoop out the seeds. I like to use a rolling pin to safely tap my knife through the squash. Cut the squash into 1/4 half moons and place them in a bowl and season them with 1 tablespoon of oil, 1/2 teaspoon of salt, a few cracks of pepper, and mix well.
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Carefully remove the hot sheets trays from the oven a place the sprouts on one pan and the squash on the other, making sure everything is in one single layer. Roast in the oven for 25 minutes and then remove the squash. Keep cooking the sprouts until they are slightly charred, about 5-10 more minutes. Once the sprouts are done remove from oven and set the oven to broil. Place the squash 8-10 inches from broiler and cook until slightly charred on both sides, flipping as needed. Remove and set aside.
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While the veggies are roasting, cut the bacon slices into small bite size pieces. Add the bacon to a medium size pan and place it over medium heat. Cook the bacon until most all the fat has rendered out and the bacon looks like it's getting crispy, about 8-10 minutes. Add the onions, garlic, walnuts, 1/4 teaspoon salt, a few cracks of pepper, and cook another 5 minutes. Lower the heat to medium-low and add the vinegar, maple syrup, mustard, and mix well. Taste for seasoning, you may need more vinegar or maple syrup. Turn the heat off the pan.
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Add the cooked sprouts and squash to a large bowl and pour over the bacon fat dressing along with 1 tablespoon of parsley. Mix very well and check for seasoning. Plate the side dish family style and garnish with more parsley, Enjoy!